JP2010505414A5 - - Google Patents
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- Publication number
- JP2010505414A5 JP2010505414A5 JP2009531385A JP2009531385A JP2010505414A5 JP 2010505414 A5 JP2010505414 A5 JP 2010505414A5 JP 2009531385 A JP2009531385 A JP 2009531385A JP 2009531385 A JP2009531385 A JP 2009531385A JP 2010505414 A5 JP2010505414 A5 JP 2010505414A5
- Authority
- JP
- Japan
- Prior art keywords
- retinyl
- linoleic acid
- linoleate
- acetate
- retinyl acetate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- OYHQOLUKZRVURQ-IXWMQOLASA-N Linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 8
- QGNJRVVDBSJHIZ-QHLGVNSISA-N retinyl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-QHLGVNSISA-N 0.000 description 8
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
- XJKITIOIYQCXQR-SCUNHAKFSA-N all-trans-retinyl linoleate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C XJKITIOIYQCXQR-SCUNHAKFSA-N 0.000 description 4
- 235000020778 linoleic acid Nutrition 0.000 description 4
- 229960000342 retinol acetate Drugs 0.000 description 4
- 235000019173 retinyl acetate Nutrition 0.000 description 4
- 239000011770 retinyl acetate Substances 0.000 description 4
- 229940071220 retinyl linoleate Drugs 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 229920001429 Chelating resin Polymers 0.000 description 2
- 229940040461 Lipase Drugs 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 108090001060 lipase Proteins 0.000 description 2
- 102000004882 lipase Human genes 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229960003471 retinol Drugs 0.000 description 2
- 235000020944 retinol Nutrition 0.000 description 2
- 239000011607 retinol Substances 0.000 description 2
- 108010084311 Novozyme 435 Proteins 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/544,152 | 2006-10-06 | ||
| US11/544,152 US7566795B2 (en) | 2006-10-06 | 2006-10-06 | Preparation of retinyl esters |
| PCT/US2007/020185 WO2008045185A2 (fr) | 2006-10-06 | 2007-09-18 | Préparation d'esters de rétinyle |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010505414A JP2010505414A (ja) | 2010-02-25 |
| JP2010505414A5 true JP2010505414A5 (fr) | 2010-09-16 |
| JP5474556B2 JP5474556B2 (ja) | 2014-04-16 |
Family
ID=38988309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009531385A Expired - Fee Related JP5474556B2 (ja) | 2006-10-06 | 2007-09-18 | 有機溶媒中でリパーゼを用いる短鎖レチニルエステル及び長鎖酸又は長鎖エステルからの長鎖レチニルエステルの製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7566795B2 (fr) |
| EP (1) | EP2082056B1 (fr) |
| JP (1) | JP5474556B2 (fr) |
| CN (1) | CN101553574B (fr) |
| ES (1) | ES2403099T3 (fr) |
| WO (1) | WO2008045185A2 (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008004725A1 (de) * | 2008-01-16 | 2009-07-23 | Evonik Goldschmidt Gmbh | Verfahren zur heterogenkatalysierten Herstellung von Carbonsäurederivaten |
| US8846723B2 (en) * | 2010-07-29 | 2014-09-30 | Eastman Chemical Company | Esters of O-substituted hydroxy carboxylic acids and preparations thereof |
| CN102363606B (zh) * | 2011-11-03 | 2013-06-19 | 厦门金达威集团股份有限公司 | 维生素a棕榈酸酯的合成方法 |
| CN104520270A (zh) * | 2012-08-07 | 2015-04-15 | 帝斯曼知识产权资产管理有限公司 | 视黄醇酯的酯交换方法 |
| KR101700909B1 (ko) | 2015-05-29 | 2017-02-14 | 주식회사 마크로케어 | 장쇄 레티닐 에스테르 제조를 위한 2상 반응 시스템 및 장쇄 레티닐 에스테르 제조방법 |
| CN105969833B (zh) * | 2016-03-17 | 2019-06-07 | 厦门金达威维生素有限公司 | 一种维生素a棕榈酸酯的合成方法 |
| PL3541783T3 (pl) | 2016-11-17 | 2024-03-04 | University Of Debrecen | Związki prekursorowe do dostarczania retinoidów szlaku witaminy a5 i ich zastosowania |
| RU2702005C1 (ru) * | 2018-12-18 | 2019-10-03 | федеральное государственное бюджетное образовательное учреждение высшего образования "Волгоградский государственный медицинский университет" Министерства здравоохранения Российской Федерации | Синтез полусинтетических производных природных лютеина и астаксантина |
| RU2739248C1 (ru) * | 2019-12-02 | 2020-12-22 | федеральное государственное бюджетное образовательное учреждение высшего образования "Волгоградский государственный медицинский университет" Министерства здравоохранения Российской Федерации | Синтез полусинтетических сложных эфиров природного зеаксантина |
| KR102518841B1 (ko) * | 2021-11-09 | 2023-04-10 | 경상국립대학교산학협력단 | 레티노이드 제조용 조성물 및 이를 이용한 레티노이드의 제조 방법 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62248495A (ja) * | 1986-04-23 | 1987-10-29 | Mihama Hisaharu | ビタミンａエステルの製法 |
| JPH0716425B2 (ja) * | 1987-05-20 | 1995-03-01 | 花王株式会社 | 油脂類のエステル交換反応方法 |
| JPH0710231B2 (ja) * | 1987-12-09 | 1995-02-08 | 花王株式会社 | 固定化酵素および固定化酵素を用いたエステル合成方法 |
| US5232843A (en) * | 1989-10-20 | 1993-08-03 | Unilever Patent Holdings Bv | Preparation of immobilized lipase by adsorption of lipase and a non-lipase protein on a support |
| JPH03183480A (ja) * | 1989-12-13 | 1991-08-09 | Ajinomoto Co Inc | 固定化リパーゼ及びこれを用いる油脂のエステル交換反応 |
| JPH061996A (ja) * | 1992-06-17 | 1994-01-11 | Asahi Denka Kogyo Kk | 油脂のエステル交換方法 |
| JP2668187B2 (ja) * | 1993-09-17 | 1997-10-27 | 日清製油株式会社 | リパーゼ粉末を用いたエステル交換法 |
| US5902738A (en) * | 1996-04-18 | 1999-05-11 | Roche Vitamins Inc. | Enzymatic acylation |
| IL134717A0 (en) * | 2000-02-24 | 2001-04-30 | Enzymotec Ltd | Method for increasing the performance of immobilized biocatalysts, and catalysts obtained thereby |
| JP3932788B2 (ja) * | 2000-09-14 | 2007-06-20 | 不二製油株式会社 | 油脂類のエステル交換方法 |
| EP1369411A1 (fr) | 2002-06-07 | 2003-12-10 | Cognis France S.A. | Compositions cosmétiques et/ou pharmaceutiques contenant des esters de rétinol |
| GB0226270D0 (en) | 2002-11-11 | 2002-12-18 | Unilever Plc | Method of producing retinyl esters |
| CN1260368C (zh) * | 2003-11-28 | 2006-06-21 | 北京化工大学 | 一种用固定化脂肪酶催化合成维生素a脂肪酸酯的方法 |
| CN100424170C (zh) | 2005-10-11 | 2008-10-08 | 北京化工大学 | 脂肪酶、其基因、产生该酶的亚罗解脂酵母及其应用 |
-
2006
- 2006-10-06 US US11/544,152 patent/US7566795B2/en active Active
-
2007
- 2007-09-18 CN CN200780037515.7A patent/CN101553574B/zh not_active Expired - Fee Related
- 2007-09-18 ES ES07838402T patent/ES2403099T3/es active Active
- 2007-09-18 WO PCT/US2007/020185 patent/WO2008045185A2/fr active Application Filing
- 2007-09-18 EP EP07838402A patent/EP2082056B1/fr not_active Not-in-force
- 2007-09-18 JP JP2009531385A patent/JP5474556B2/ja not_active Expired - Fee Related
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